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1-Fluoro-3-iodo-2-nitrobenzene (2.67 g, 10 mmol; Apollo) and methylamine (2.87 g, 27% w/w solution in MeOH) were dissolved in MeOH (50 ml.) and stirred at RT overnight. The mixture was concentrated to afford the title compound (2.22 g) as a red solid.
5-hydroxy-2-(4-hydroxybenzoyl)-3-(4-hydroxyphenethyl)-1,4-bis(4-hydroxyphenyl)-3,6-dihydropyrrolo[2,3,-c]carbazol-7-yl 2,2,2-trichloroethyl sulfate[ No CAS ]
With potassium tert-butylate; In toluene; at 20℃; for 2h;
Potassium tert-butoxide (92 mg, 0.824 mmol) was added portionwise over 5 mm to a solution of <strong>[886762-71-6]1-fluoro-3-iodo-2-nitrobenzene</strong> (200 mg, 0.749 mmol) and EtOH (0.052 mL, 0.90 mmol) intoluene (3 mL), then the mixture was stirred at RT for 2 h. FCC (toluene) afforded the title compound as a colourless solid (247 mg, assume quantitative). ?H NMR (CDC13) oe 7.41 (1H, d), 7.10 (1H, t), 7.00 (1H, d), 4.13 (2H, q), 1.40 (3H, t).
With potassium carbonate; In toluene; at 85℃; for 3h;
To a solution of <strong>[886762-71-6]1-fluoro-3-iodo-2-nitrobenzene</strong> (228 mg, 0.854 mmol) in toluene (3 mL) was added potassium carbonate (177 mg, 1.28 mmol) and morpholine (1 mL). The mixture was heated at 85 C for 3 h. The cooled reaction mixture was evaporated and the residue partitioned between EtOAc and water. The aq. phase was extracted with more EtOAc, and the combined organic extracts were washed with water, then brine, dried (Na2SO4) and concentrated in vacuo to leave a residue. FCC (20-50% EtOAc in isohexane) gave the title compound as a light yellow solid (168 mg, 59%). M/z 335 (M+H).
With tert.-butylnitrite; iodine; In acetonitrile; at 20 - 60℃; for 18h;
To a pre heated solution of iodine [244.23 g, 1923.1 mmol] and tert butyl nitrite [1 14.2 ml, 961.5 mmol] in MeCN (300 mL) at 60 C, was added a solution of compound 1 [30.00 g, 192 3 mmol] in MeCN (300 mL). The reaction mixture was stirred for an additional 2 h at 60 C and allowed to stir at room temperature for another 16 h. After completion [ monitored by TLC [10% EtOAc-Hexane, Rf=0.5], the mixture was quenched with saturated aqueous Na2S2C>3 [300 mL] solution at ice cool condition and extracted with EtOAc [3x500 mL] The combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography using 0-3 % EtOAc-hexane as eluting solvent to afford compound 2 [39 g, 7614] as a yellow solid. [Tl NMR is consistent].
{(S)-1-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl}carbamic acid tert-butyl ester[ No CAS ]
{(1S,8S)-9-oxo-1-[(1H-[1,2,3]triazol-4-ylmethyl)carbamoyl]-1,2,8,9-tetrahydro-7H-6-oxa-9a-azabenzo[cd]azulen-8-yl}-carbamic acid tert-butyl ester[ No CAS ]
(1S,8S)-8-amino-9-oxo-1,2,8,9-tetrahydro-7H-6-oxa-9a-aza-benzo[cd]azulene-1-carboxylic acid (1H-[1,2,3 ]triazol-4-ylmethyl)amide trifluoroacetate[ No CAS ]
(1S,8S)-8-((2S,3S)-2-benzoylamino-3-methyl-pentanoylamino)-9-oxo-1,2,8,9-tetrahydro-7H-6-oxa-9a-aza-benzo[cd]azulene-1-carboxylic acid (1H-[1,2,3]triazol-4-ylmethyl)amide[ No CAS ]
{(8R)-6,6,9-trioxo-1-[(1H-[1,2,3]triazol-4-ylmethyl)-carbamoyl]-1,2,6,7,8,9-hexahydro-6λ6-thia-9a-aza-benzo[cd]azulen-8-yl}carbamic acid tert-butyl ester[ No CAS ]
(8R)-8-amino-6,6,9-trioxo-1,2,6,7,8,9-hexahydro-6λ6-thia-9a-aza-benzo[cd]azulene-1-carboxylic acid (1H-[1,2,3]triazol-4-ylmethyl)amide trifluoroacetate[ No CAS ]
(1S,8R)-8-{(2S,3S)-2-[2-(2-fluoroethoxy)acetylamino]-3-methyl-pentanoylamino}-6,6,9-trioxo-1,2,6,7,8,9-hexahydro-6λ6-thia-9a-aza-benzo[cd]azulene-1-carboxylic acid (1H-[1,2,3]triazol-4-ylmethyl)amide[ No CAS ]
(3S,6S)-3-tert-butoxycarbonylamino-4-oxo-6-[(1H-[1,2,3]triazol-4-ylmethyl)carbamoyl]-3,4,6,7-tetrahydro-2H-[1,4]diazepino[3,2,1-hi]indole-1-carboxylic acid benzyl ester[ No CAS ]
(3S,6S)-3-amino-4-oxo-6-[(1H-[1,2,3]triazol-4-ylmethyl)-carbamoyl]-3,4,6,7-tetrahydro-2H-[1,4]diazepino[3,2,1-hi]indole-1-carboxylic acid benzyl ester trifluoroacetate[ No CAS ]
(3S,6S)-3-{(2S,3S)-2-[2-(2-fluoroethoxy)acetylamino]-3-methyl-pentanoylamino}-4-oxo-1,2,3,4,6,7-hexahydro-[1,4]diazepino[3,2,1-hi]indole-6-carboxylic acid (1H-[1,2,3]triazol-4-ylmethyl)amide[ No CAS ]
[(S)-6-(tert-butyl-dimethylsilanyloxymethyl)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[3,2,1-hi]indol-3-yl]carbamic acid tert-butyl ester[ No CAS ]
{(3S,6S)-1-methyl-4-oxo-6-[(1H-[1,2,3]triazol-4-ylmethyl)carbamoyl]-1,2,3,4,6,7-hexahydro-[1,4]diazepino[3,2,1-hi]indol-3-yl}carbamic acid tert-butyl ester[ No CAS ]
(3S,6S)-3-amino-1-methyl-1,2,3,4,6,7-hexahydro-[1,4]diazepino[3,2,1-hi]indole-6-carboxylic acid (1H-[1,2,3]triazol-4-ylmethyl)amide trifluoroacetate[ No CAS ]
(3S,6S)-3-{(2S,3S)-2-[2-(2-fluoroethoxy)acetylamino]-3-methyl-pentanoylamino}-1-methyl-4-oxo-1,2,3,4,6,7-hexahydro-[1,4]diazepino[3,2,1-hi]indole-6-carboxylic acid (1H-[1,2,3]triazol-4-ylmethyl)amide[ No CAS ]
(S)-2-tert-butoxycarbonylamino-3-(3-iodo-2-nitro-phenoxy)propionic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
47.6%
To a stirred suspension of NaH (50%) [3.60 g, 74.9 mmol] in DMF [60 mL] was added slowly a solution of compound 3 [15.3 g, 74.9 mmol] in DMF [30 mL] maintaining the external temperature below -10 C. After addition, reaction mixture was left stirring vigorously for half an hour under cold condition. A solution of compound 2 [20.0 g, 74.9 mmol] in DMF [30 mL] was slowly added to the reaction mixture under ice cold condition, after addition reaction mixture was allowed to warm at room temperature and stirred for 16 h. Then reaction mixture was quenched with water [500 mL] and aqueous part was extracted with EtOAc [2x100 mL j. Organic part was separated; pH of the aqueous part was slowly adjusted to 2-3 using IN aqueous HC1 under ice cooled condition and immediately extracted with EtOAc [2x300 ml]. Organic part was separated, dried (MgS04) and concentrated under reduced pressure to afford 7.2 g of compound 4. 15 g of un-reacted starting material was also recovered; this material was further treated under the same condition to afford 8.5 g compound 4 [total 16.1 g, 47.6 %]. Mass [ESI]: m/z 452.21 [MM]
(R)-2-tert-butoxycarbonylamino-3-(3-iodo-2-nitro-phenylsulfanyl)propionic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
43%
NaHCOs [5.70 g, 67.8 mmol] was added to a stirred solution of compound 3 [5.00 g, 22.6 mmol] in water (30 mL) at room temperature under argon atmosphere and stirred for 10 minutes. Finally, solution of compound 2 [4.22 g, 15.8 mmol] in EtOH (40 mL) was added to the reaction mixture and stirred at 80 C for 4 h. After completion, solvent was evaporated, crude was diluted with water [200 mL] and extracted with Et?.0 [200 mLj. Organic part was separated; pH of the aqueous part was slowly adjusted to 2-3 using 1 (N) aqueous HC1 under ice cooled condition and immediately extracted with EtOAc [2x100 mi]. Organic part was separated, dried [Na2SQ4] and concentrated under reduced pressure to afford compound 4 [4.5 g, 43%]. Mass [ESI]: m/z 468.27 [M++l ]
(S)-2-tert-butoxycarbonylamino-3-(3-iodo-2-nitro-phenylamino)propionic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
68.4%
K2CO3 [5.20 g, 37.7mmoi] was added to a stirred suspension of compound 3 [7.0 g, 34 mmol] in EtOH (230 mL) under ice cold condition. After addition reaction mixture was left to stir vigorously for half an hour under cold condition. Finally, compound 2 [9.16 g, 34.3 mmol] was added portion wise to the reaction mixture at 0 C, after addition reaction mixture was brought to room temperature and heated at 80 C for 40 h. After completion, EtOH were evaporated, crude was diluted with water [200 mL] and extracted with EI2O [200 L] Organic part was separated; pH of the aqueous part was slowly adjusted to 2-3 using 1 (N) aqueous HC1 under ice cooled condition and immediately extracted with EtOAc [2x200 mL] Organic part was separated, dried [MgSOr] and concentrated under reduced pressure to afford compound 4 [10.6 g, 68 4 %] as dark red floppy solid. Mass [ESI]: ra/z 451.21 j .1 - l 1.
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